Methyl chloroglyoxylate → Methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-methyl-3-[(phenylmethyl)amino]butanoate (5.5853 g, 25.24 mmol) in THF (125 mL) was added N,N-diisopropylethylamine (6.6 mL, 37.89 mmol). The solution was cooled to 0° C., and methyl chloro(oxo)acetate (2.55 mL, 27.73 mmol) was added dropwise. The mixture was then allowed to stir and warm to room temperature overnight. The mixture was diluted with EtOAc (200 mL) and washed with 1 N aq. HCl (100 mL), followed by sat. aq. NaHCO3 (100 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was crystallized from EtOAc—hexanes to give a white solid that was collected by vacuum filtration and washed with hexanes. The resulting methyl 3-methyl-3-[[(methyloxy)(oxo)acetyl](phenylmethyl)amino]butanoate (7.0709 g, 91%) was obtained as a white solid. LCMS: (M+H)+: 308.1.

Provenance & Evidence